Water → HCID 12851833, compound

HRID 1156871Notes

Reaction equation

HRID 1156871 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18]O)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O.O.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18][Cl:22])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 128518321-(4-Bromophenyl)-5-hydroxymethylisoquinoline

Product 1

HCID 12851833HCID 12851833, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Bromophenyl)-5-hydroxymethylisoquinoline (17 g) was dissolved in 300 ml of tetrahydrofuran, and 15 ml of phosphorus oxychloride was added. The mixture was stirred at room temperature for 1 hour. After the reaction, water was added, and the reaction mixture was neutralized with an aqueous solution of sodium hydroxide. The mixture was extracted with benzene, and dried. The solvent was distilled off. The residue was recrystallized from ether-hexane to afford 13.2 g of 1-(4-bromophenyl)-5-chloromethylisoquinoline as colorless prisms having a melting point of 115.5° to 118.5° C.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with benzene
  3. customdried
  4. distillationThe solvent was distilled off
  5. customThe residue was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-c9da68286df54d1c92ed69eaca25b59c
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…